Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Apartment in Bennington

4.94 out of 5 average rating, 154 reviews

NEW Escape the City- Vermont Studio

Our newly renovated studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Green Mountain National Forest. It's on the second floor of our home through a private entrance with a personal deck and outdoor seating. Take an afternoon to stroll to the Mile Around Woods, or hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Feb. 10 – 17

$145 CAD per night
Superhost

Cottage in North Bennington

4.9 out of 5 average rating, 288 reviews

Romantic Private Vermont Cottage - Waterfront

Welcome to beautiful Southern VT! This is a private cottage located in Bennington, VT. The setting is picturesque, on a private lake with diverse wildlife, waterfall and covered bridge. Full kitchen, covered porch, loft bedroom and additional sofa bed. We provide every conceivable amenity for a comfortable stay. A unique retreat for a cozy and peaceful getaway. There is no other vacation property of this quality and character in southern Vermont. Enjoy mornings on your own private lake.

May 16 – 23

$266 CAD per night
Guest favourite

Cabin in Shaftsbury

4.99 out of 5 average rating, 199 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Jan. 21 – 28

$575 CAD per night

Popular amenities for Bennington vacation rentals

Stay near Bennington's top sights

Bennington Battle Monument72 locals recommend
The Blue Benn40 locals recommend
Madison Brewing Company Pub & Restaurant42 locals recommend
Ramunto's Brick Oven Pizza16 locals recommend
Apple Barn Country Bake Shop10 locals recommend
Sunny Side Diner3 locals recommend

Other great vacation rentals in Bennington

Guest favourite

Tiny homes in Wilmington

4.98 out of 5 average rating, 128 reviews

Beautiful Timber Frame Retreat

Sep. 11 – 18

$324 CAD per night
Guest favourite

Guest suite in Wilmington

4.92 out of 5 average rating, 708 reviews

Architectural GuestSuite

May 30 – Jun. 6

$182 CAD per night
Guest favourite

Apartment in Petersburg

4.85 out of 5 average rating, 143 reviews

The Beer Diviner Brewery Apartment

Aug. 29 – Sep. 5

$101 CAD per night
Guest favourite

Tiny homes in Jamaica

4.94 out of 5 average rating, 1136 reviews

Apple Blossom Cottage: A Tiny House

Oct. 15 – 22

$158 CAD per night
Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 260 reviews

The Studio With a View. Bring your dog, too!

Oct. 16 – 23

$227 CAD per night
Guest favourite

Apartment in Stamford

4.86 out of 5 average rating, 269 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Sep. 9 – 16

$214 CAD per night
Guest favourite

Guesthouse in Williamstown

4.96 out of 5 average rating, 142 reviews

Brookside Cottage

Jun. 18 – 25

$209 CAD per night
Guest favourite

Cabin in Woodford

4.91 out of 5 average rating, 131 reviews

Lakeview Cabin in the Mountains - beautiful

Oct. 26 – Nov. 2

$288 CAD per night
Guest favourite

Home in Shaftsbury

4.92 out of 5 average rating, 96 reviews

Cheerful 1 bedroom cottage

Sep. 27 – Oct. 4

$135 CAD per night
Superhost

Cabin in Bennington

4.81 out of 5 average rating, 99 reviews

Vermont Cabin - Secluded Woods on South Stream

Apr. 29 – May 6

$181 CAD per night
Guest favourite

Farm stay in Bennington

4.96 out of 5 average rating, 77 reviews

The Farm cottage

Oct. 31 – Nov. 7

$242 CAD per night
Guest favourite

Apartment in Bennington

4.86 out of 5 average rating, 37 reviews

Cozy Loft steps from VT downtown

Dec. 18 – 25

$223 CAD per night

Quick stats about vacation rentals in Bennington

Total rentals

40 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.9K reviews

Nightly prices starting at

$41 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Bennington